The present invention relates to novel amine derivatives having the general formula (I): ##STR5## wherein X is selected from the group consisting of ##STR6## wherein Q is oxygen, sulfur or nitrogen atom, and ##STR7## wherein Q is as above; Y is selected from the group consisting of ##STR8## R.sup.1 is hydrogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms, preferably having 1 to 4 carbon atoms; R.sup.2 is hydrogen atom or linear or branched alkyl group having 1 to 6 carbon atoms, preferably having 1 to 4 carbon atoms; R.sup.3 is hydrogen atom, a halogen atom such as fluorine, chlorine, bromine and iodine, or a linear or branched alkyl group having 1 to 6 carbon atoms, preferably having 1 to 4 .carbon atoms; R.sup.4 is hydrogen atom, a linear or branched alkyl group having 1 to 10 carbon atoms, preferably having 1 to 7 carbon atoms, cycloalkyl group having 3 to 7 carbon atoms, preferably having 5 to 6 carbon atoms, halogenated alkyl group such as trifluoro methyl group, or a halogen atom such as fluorine, chlorine, bromine and iodine; R.sup.5 is hydrogen atom, a linear or branched alkyl group having 1 to 6 carbon atoms, preferably having 1 to 4 carbon atoms, a linear or branched alkoxy group having 1 to 6 carbon atoms, preferably having 1 to 4 carbon atoms, a halogen atom such as fluorine, chlorine, bromine and iodine, nitro group or hydroxy group; R.sup.5 is attached to an arbitrary position of X, and R.sup.3 or R.sup.4 is attached to an arbitrary position of Y, processes for preparing the same and fungicides containing the same as an effective component.
The acid addition salts of said amine derivatives having general formula (I) are, for instance, hydrochloride, hydrobromide, sulfate, nitrate, acetate, oxalate, tartrate, benzenesulfate, methanesulfate and the like, which are pharmacologically acceptable.
The compounds according to the present invention can be prepared, for instance, by the process (a) which comprises reacting the compound having the general formula (II): ##STR9## wherein R.sup.1, R.sup.5 and X are as above, A is an eliminating group or R.sup.2 --NH-- wherein R.sup.2 is as above, with the compound having the general formula (III): ##STR10## wherein R.sup.3, R.sup.4 and Y are as above, A is an eliminating group or R.sup.2 --NH--, wherein R.sup.2 is as above, and A is different from that of formula (II) or the process (b) which comprises reducing the compound having the general formula (IV): ##STR11## wherein R.sup.3, R.sup.4, R.sup.5, X and Y are as above, W is ##STR12## wherein R.sup.1 and R.sup.2 are as above, and by collecting the obtained product from the process (a) or the process (b) in the form of a free base or an acid addition salt.
The above-mentioned processes (a) and (b) can be carried out in the conventional manner.
The process (a) can be carried out in the reaction solvent of aromatic hydrocarbon such as benzene and toluene, ether such as diethyl ether and dioxane, or carboxylic acid alkyl amide such as dimethylformamide at a reaction temperature ranging from room temperature to a boiling point of the solvent, preferably from room temperature to 60.degree. C. Examples of eliminating group A are a halogen atom such as chlorine and bromine, organic sulfonyloxy group having 1 to 10 carbon atoms such as tosyloxy and mesyloxy. The reaction is advantageously carried out in the presence of reagent binding with acid, i.e. hydroxide of alkali metal or alkaline earth metal, or carbonate of alkali metal or alkaline earth metal such as sodium carbonate and potassium carbonate.
The process (b) can be carried out in an inactive solvent of ether such as diethyl ether, tetrahydrofuran and dioxane at room temperature or a reaction temperature ranging from room temperature to a boiling point of the solvent, using lithium aluminum hydride as a reducing agent.
The reaction to convert the compound of the present invention having the general formula (I) from its free base into its acid addition salt, or from its acid addition salt into its free base, can be carried out in the conventional manner.
The compounds having the general formula (II), (III) or (IV) which are the starting materials and used for preparing the compound of the present invention having the general formula (I) can be produced easily in the conventional manner whether or not they are known or novel compounds. Examples of preparing them are as follows: ##STR13## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, X and Y are as above.
The reaction may be carried out under such conditions as usually employed in such reaction and various intermediates can be subjected to further reaction without isolation. In case that isolation is necessary, it can be carried out by the conventional process.
The compounds of the present invention show an excellent antifungal activity. They show an antifungal activity at the concentration of 0.003 to 100 .mu.g/ml in vitro especially against such fungi as Trichophyton mentagrophytes, Trichophyton interdigitale, Trichophyton rubrum, Microsporum canis, Microsporum gypseum, Epidermophyton floccosum, Cryptococcuss neoformans, Sporothrix schenekii, Aspergillus fumigatus and Candida albicans. In vivo test of dermatomycosis model employing guinea pig (see Sumio Sakai: Shinkin To Shinkinsho, vol. 1, page 252, 1960) also ascertained that the compounds of the present invention have an excellent antifungal activity.
The compounds of the present invention can provide fungicides in the form of liquid preparation, ointment, cream and the like. Though an amount of an effective component may vary depending on species of fungi, a degree of disease, a kind of the compound employed, dosage form, and the like, generally the compounds of the present invention can provide fungicides at a concentration of 0.01 to 5%.